


Typical Day

by Bookoholic



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Anal Sex, Bar/Pub Trope, Bisexual Dean Winchester, M/M, Panty Kink, Pool hustling
Language: English
Status: Completed
Published: 2019-06-28
Updated: 2019-06-28
Packaged: 2020-05-28 15:24:17
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,731
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19396927
Author URL: https://archiveofourown.org/users/Bookoholic/pseuds/Bookoholic
Summary: Ever have one of those works days where you just want to go somewhere to sit and relax, have a drink, and forget that it ever happened?Dean has, but he's not going to forget this one for a long time.





	Typical Day

**Author's Note:**

> Inspired by a Facebook Prompt. I hope you like it!

Music blared through the speakers of the jukebox in the corner of the nearest bar Dean could find.

Planting himself in the first open bar stool, Dean ordered a double of whichever whiskey they had in stock and down it in one swig. Ignoring the bartender’s raised eye brow, Dean offers his glass for another round.

“Hard day?” the bartender asked.

Dean blew his cheeks out watching his glass get filled, “You have no idea.”

Dean works a nine-to-five job as a mechanic. He’s damn good at it, but the universe seemed to have it out for him on this day specifically. Working on six cars in the Kansas summer heat isn’t the greatest experience in the world; especially when he spilled nearly an entire tank of black oil all over the place from a rusted out Ford, dropped a heavy tool kit on his foot, hit his head on a bumper while trying to slide out from underneath an Audi, and sat there listening to a crazed fucker screaming at him for putting a scratch on his car that Dean knows was already there when the douche drove it in. 

After he clocked out, Dean went home, scrubbed as much of the day away that he could in a very much needed shower, then drove in the cool night air to the nearest bar to drink away the rest of it. 

Now on his third drink, he’s starting to feel loose enough to relax. Looking around he catches the eye of a couple of women at the bar or tables and he lifts his glass, politely acknowledging them, but he’s not really feeling up to it. 

Not now at least, since his desire to be as comfortable and relaxed as possible comes with a deep secret he’s vowed to keep to himself until he’s six feet under. 

Sighing as the tension slowly leaves his body, Dean swigs the rest of his whiskey and lifts his glass for another, when suddenly some guy bursts through the front door and makes a beeline straight for the bar. As the bartender pours Dean’s drink, the man sits two stools away from him and places a twenty on the counter. 

“What can I get ya?” the bartender asked.

The man takes a moment to eye the stock at the counter, “I need something strong enough to forget the burn of spilt coffee on my arm from trying to carry several stacks of project proposals that I’ve worked on for two weeks with no sleep that never even got a second glance because my boss is a two-faced son of a bitch.”

As the bartender stared dumbfounded at the man, “Um.”

Dean cleared his throat and lifted his glass, lightly tapping it when the man looked at him. “Right here.”

“Yes. That please.” he gestured to Dean.

As the bartender set him up, Dean took a sip of his own drink and watched the man take his glass to observe it for a moment before slowly chugging it. 

Dean’s eyebrows rose in amusement as the man’s face started to twist in disgust. When finished, the man coughed as the burn settled in his throat. Blue eyes tearing up, he offered his glass again. “Another, please.”

Dean chuckled to himself at the man’s antics and raised his own glass in offering. The man briefly looks at Dean’s offered toast before he clinks his against it and they take a sip together. Sitting in silence, Dean nonchalantly glances at the man next to him and gives him a once over. Tall, dark unruly hair with a five o’clock shadow on a sharp jawline, what dean can only guess is a nicely toned body underneath a full three-piece suit with large tan trench coat, and a nice set of blue eyes that match the loose tie around his neck. All in all, the guy was quite the looker. 

Dean doesn’t explore the other side of his sexuality very often, but when he does, he’s careful to make sure the guy’s up for it before he makes an offer. Especially when he’s at an old seedy bar instead of the gay bar across town. 

Lost in his own thoughts, he doesn’t notice the man taking glances at him as well until the guy asks a question. 

“Bad day as well?” 

Dean laughed to himself and nodded, “Ooh yeah. Maybe not as bad as yours though.” He takes a sip, “Your boss sounds like a dick.”

The man chuckles, “Appropriate, considering that’s his name.” 

Dean smiled as he chucked with him. 

The man extended his hand to Dean, “Castiel.”

Dean turned to reached over and grasp it, “Dean Winchester.”

The man, Castiel, takes another sip of whiskey with a pinched face, “So, what brings you here, Dean?” He asked.

Dean waves his hand about, his head buzzing from his fourth drink. “A whole lotta bullshit in a short amount of time. Nothing a few drinks can’t cure.” He demonstrates by taking another sip. 

Castiel mirrors him before he sighs and rolls his neck, popping it. Dean holds in a slight shiver when the man groans in relief. Glancing around the bar for the first time, Castiel spots a pool table in the back and chugs the rest of his drink. Grimacing as he feels it burn down his throat, he still offers his glass for a refill. 

“Do you know how to play?” 

Dean looks at him in question and Castiel nods towards the pool table. Dean has to hold his smirk. Ever since he was a teenager, he played pool in every bar he came across, learning tricks, taking the perfect shot, and even found out how to make money from it. He‘s damn good at that too. 

“I dabble every now and then.” He comments, sipping his drink to hide his smirk.

“Well then, after a day like this, I’m feeling the urge to hit something with a stick. Considering the alternative may send me to prison, this seems like the next best thing. Care to join?” Dean snorts a laugh into his drink.

“Well Cas, when you put it that way.” Castiel straightens up with a smile and heads towards the pool table, discarding his trench coat as he goes. 

Refilling his glass, Dean watches Castiel round the pool table to find the cue balls and triangle to set it up. It may be the alcohol, but Dean feels a burn whenever Castiel bends over. 

Looking away, he sighs and takes another sip of whiskey. He’s too horny to think clearly right now, the man’s probably straight and just looking for a bar buddy. 

_But,_ his traitorous dick jumps in, _it wouldn’t hurt to check._

Dean took a deep breath and ran a hand through his hair before getting up to leisurely walk towards the pool table. Every step reminding him of what hides beneath. 

Somehow it boosts his confidence because he _knows_ he looks good.

Castiel racks the balls together and settles them in place. Dean sets his drink down onto a nearby table and walks over to the pool cues. He watches Castiel from the corner of his eye, making sure he’s looking before he runs his fingers gingerly down the length of the stick as slowly as he could before he picks one at random.

He catches that Castiel looks pointedly away from him with a flush in his face, but that could just be the alcohol. He can’t jump to conclusions, he learned that lesson the hard way. 

“You know Cas, why don’t we make it interesting?” 

Cas looks at him intrigued as he takes a drink. Dean keeps his eyes on Castiel as he pulls a twenty from his pocket and sets it on the edge of the pool table. “Winner takes all.”

Cas considers it for a moment before he pulls a twenty from his own pocket and sets it on top of Dean’s. Dean is testing the waters here with Cas, but if he’s wrong, he’s not walking out of here empty handed. 

So, he takes it slow; he bends over more than necessary to “line up his aim” before he takes his shots. He trails his fingers across the edge of the table in front of Castiel’s sight to see if he can distract him, hiding his smile when it works. Dean had even gone so far as to stand in front of Castiel and bend over to take a shot. He actually felt sure of himself when Castiel didn’t necessarily move out of the way. 

He dares to say he even felt Cas brush up against him.

Each game they play, Dean lets Cas win to boost his ego, but each time losing twenty dollars. He’s also not getting any closer to being 100% positive that Cas is free game. He’s usually pretty good at this, but Cas is a hard one to crack. After his last shot, Dean started to weigh his options: despite being so sure that the guy would be game for continuing the night at his place, he hesitates because Cas hasn’t made a move to show he’s interested. Either he’s the biggest gentleman on the planet or he’s straight. Either one doesn’t exactly skew in the direction he wanted to go tonight which doesn’t help his libido in the slightest. 

Coming to a decision, he starts his final act.

“Alright, one more game. One more! High stakes this time.” He pulls out two more twenty’s and place them on the table. Castiel, confident from winning three games and tipsy from drinking more than he’s used to, pulls out forty dollars and sets it down without a second thought. 

“That might not have been the best decision in on your part, Dean.” He notes.

Dean smirks at him, “Well, who knows. I might get lucky this time.”

Castiel sets the balls in place as Dean sets up for his shot. Once he’s clear, Dean let’s his shot go and smiles when two solids go in right away. Cas stands there looking slightly amazed and confused at the same time. 

Dean rounds the table, slapping Cas’ arm as he walks by, “See? All you need is a little luck.” 

Castiel eyes him carefully as Dean lines up his shot for another ball and hits it right into the pocket. “Yes, luck indeed.” He mutters.

Castiel did have one chance to make a shot, but he was nowhere near Dean’s level of skill so when he missed, Dean took the game. 

Castiel doesn’t seem surprised that he ultimately lost as he sips his whiskey. His throat all but numb to the burn now. Dean smugly grins at as the eight ball sinks in the pocket and secured his winnings.

As he straightened up, the bartender calls to them, “Sorry guys, we’re closing up in a few here.” 

Dean checks his watch to see it’s almost 1am, so he turns to Castiel with a grin. “Well you played some good games buddy, but I guess Lady Luck was on my side tonight.” He says as he holds the money up tauntingly.

Castiel quirks an eyebrow at him, “So it would seem.”

Dean grabs his drink and clinks it against Cas’ before he downs the rest of it. Wiping his mouth, Dean sets the glass on the bar counter before slapping Cas’ back, “See ya buddy, thanks for the games.”

Castiel watches Dean walk out the door before he grabs his own drink and downs it in one gulp.

Dean walks down the side ramp towards the back where his car is parked. The moment he entered the darkened alley he felt a someone grab him and push him up against the side of the bar. Dean can handle himself against assholes or petty thieves, but he was a bit taken by surprise to find that it was Cas holding him there instead.

Dean could smell the whiskey on Cas’ breath his face was so close. Castiel didn’t appear to be royally pissed or even angry as he looked from Dean’s eyes straight to his lips. 

Fuck, he is so happy he was wrong. 

Dean licked his lips in response as Cas looked back into his eyes.

“I do believe you hustled me, Mr. Winchester.”

Oh shit, that deep voice ran straight to his loins.

Dean managed to smirk lewdly in response, “I don’t know what you’re talking about, Cas.”

Castiel looked back down to his lips, “I know that you do.”

Dean kept his eye on Cas’ own lips as he spoke, “Yeah? What are you gonna do about it?”

Castiel leaned in closer to where their noses nearly touched. “That’s up to you, Dean.”

Dean swallowed at the baritone voice as he kept his eye’s on Cas’ lips. 

“Because I would do _everything_ to you.”

Dean involuntarily let out a groan as his mouth fell open. Cas took his chance and pressed his body against Dean into the wall as he kissed Dean.

Dean pressed back and grabbed onto the oversized trench coat as Cas kissed him like a starving man. They broke for air every now and then, but always dove back in for more. 

So entangled in each other, they fail to hear the door of the bar open and shut until heavy footsteps start coming down the ramp around the corner. Both men freeze as they hear the bartender whistle as he starts making his way down the alleyway. Castiel nor Dean make any sort of movement as they know they’re fairly hidden in the dark cast of the building’s shadow. If they’re quiet the bartender won’t notice them. Dean has a better view then Cas of the bartender walking towards them, so he notices that the man is more focused on his cellphone than his surroundings and Dean takes advantage of that.

He gently lets go of Cas’ coat only to grab at his growing erection through his slacks. Dean was impressed Cas didn’t make a sound, rather he jolted and grabbed Dean’s had to stop him and try to move it, but Dean was very insisting. Castiel glared hard at Dean’s smug face before he ground forward into Dean’s hips hard. Dean’s eyes rolled to the back and he tilted his head back to hit the wall as hot pleasure surged through his cock. He bit his lip to keep quiet as the bartender passed them by. Cas turned his head to watch the man walk by when Dean’s finger trailed down Cas’ cock and started rubbing at the tip through his trousers. Castiel’s breath hitched and he pressed into Dean to try stop his hand from moving, but it was useless. Dean just kept rubbing his covered slit in circles watching those blue eyes start to flutter and lose focus. Cas tried to keep his breathing steady as each rub of his pants against his cock went straight up his spine. 

When Castiel finally heard a car start, he ripped Dean’s hand away and pulled his hips forward to start grinding harshly against him. Dean’s laugh ended in low groan as he spread his legs wider to give Cas more space. He held on as Cas groped his ass to keep the rhythm going. God, he didn’t care if Cas wanted to fuck or frot against the wall, he just wanted to come. It’s been way too long. 

Castiel trails his hand to the front of Dean’s pants to message Dean’s cock making the man surge his hips forward in a moan. He let him rut against his hand before he pulled the belt open and popped the button of Dean’s jeans to push his hand inside. 

Dean felt momentarily confused as to why Cas suddenly stopped. He looked back down at the man and suddenly felt cold. How could he fucking forget?

Castiel was still as he softly caressed the smooth fabric of what he can only assume are satin panties. But they couldn’t be. There was no way Castiel was this fucking lucky. 

He had to know.

He ripped his hand out of Dean’s pants, but before Dean could say anything he was turned around and pressed against the wall as his jeans were yanked down. His shiver should have been from the cold air on his ass, but it was more from Cas kneeling down and fondling at his cheeks. Dean jolted upright as he felt Cas start to bite and suckle at the fleshy mounds. Pressed against the wall Dean desperately tried to grab onto something, anything as Cas started to trail lower. He was so fucking glad he took a shower before this because Cas goes right between his legs to nip at his barely covered ball sack and chode. Leaned against the wall, he starts to lose focus and apparently his control as the alley starts to echo the moans and whimpers that escape his slacked open mouth. 

He feels Cas pull away from him for a moment, letting Dean gather his thoughts for a second before he’s back mouthing at Dean’s bare cheek. Dean feels his skin light on fire as he feels two fingers pull his panties aside and probe at his rim. 

“Fuck, yes.” He groans as he presses back into them.

Castiel chuckles as he pushed past the tightened ring of muscle and starts to wriggle deep inside Dean, stretching and massaging the inner walls. Dean fights the squirm at Cas’ prodding until that bastard finds his prostate and starts rubbing at it hard. The sensation takes him by surprise making him let out a sharp whine as his ass clenches around Cas’ fingers. Cas groans in arousal with his face resting against Dean’s ass as he watches his own fingers take Dean apart. 

Dean wants to spread his legs wider but his pants are still around his knees. He curses against the wall and can feel the chafe burn on his face from rubbing against the brick. 

“C’mon Cas.” He pleads as his groin starts to tighten up. 

Cas nuzzles Dean’s ass before he pulls his fingers out and stands up to unbuckle his own pants. Dean heard the zipper behind him and insistently pushes his hips out as the sound of a condom wrapper is torn open. He impatiently waited as he felt hands spread his cheeks, the pull of his panties pushed aside, and the hot thick tip of Cas’ cock press at his hole. Dean braced against the wall, relaxing his muscles as much as he could as Cas pushed forward. 

Once Castiel popped through, he slowly sheathed himself until he was pleasantly flush with Dean. Horny and impatient, Dean smiled in relief as his eyes flutter closed at Cas filling him up. He clenched around Cas, feeling the cock twitch inside him and an appreciative hum sound from behind his head. Castiel feels his brow sweat as he gives Dean time relax a bit more, straining to resist fucking into the tight heat, but he keeps faltering every time Dean clenches around him. That’s he then notices Dean side eyeing him with a sly grin; he’s teasing him. 

Castiel snapped his hips and felt his own grin form as Dean choked on a moan. Gripping Dean’s shoulder and hip, Castiel started thrusting into Dean building up to a quick pace. Dean’s breathing became harsh with every thrust, every pull, every brush against his prostrate. 

Damn, Cas fucks so good. 

When Cas started to speed up spastically, he wrapped his arm around Dean’s shoulders and pulled him back to his chest; hips harshly pounding against Dean’s backside. Dean reached behind him and ran his hand through Cas’ dark, thick hair and rolled his head back onto his shoulder. His breathy moans getting louder at each hard thrust. 

Castiel groaned as he felt his release building, so he started nipping and mouthing Dean’s neck. He wanted Dean to remember this night for a long time. 

He raised his head to mouth at Dean’s ear, “So good, Dean.” His breath tickling Dean’s soft lobe. “Here I thought I wouldn’t have a chance with a man like you, but look at you now.” Dean have a low moan.

Castiel rubbed at the front of Dean’s panties where his cock was peeking out, soaked with precome. Dean twitched in his hold at the sudden stimulation on his cock and groaned loudly. 

“Are you close? It’s a shame to ruin such pretty panties.” 

Dean clenches up, causing Cas to hitch and falter his thrusts, as he turns his head towards him, breathlessly whispering, “I have more.” 

Cas groaned a curse into Dean’s shoulder and came hard. 

Dean’s mouth fell open in a soundless moan, arching away from Cas as he felt the cock inside him pulse and twitch making him come all over his stomach and, effectively, ruining his panties. 

Dean slowly closed his eyes as he tried to catch his breath, letting Cas continuously grind slowly inside him chasing his climax. Cas started planting lazy kisses from Dean’s shoulder to his neck making him huff a laugh at the tickle before turning his head to start a deep make out session. 

He shivered when he felt Cas slip out of him and his empty hole try to clench around something. 

Cas lifted his head up and stared at Dean with a soft gaze, “Are you alright?” 

Dean offered a grin in return, “More than alright.” 

Cas pulled him in for another very passionate kiss before he let go and stepped back. As Dean gained his balance and reached down to pull his pants up, Cas pulled off the condom and tossed it in a nearby trash can before tucking himself back in his pants. 

Dean turned around and rolled his shoulders, popping his neck, before leaning back onto the wall where he was thoroughly fucked against and eyed the man in front of him, biting his lip. 

Cas was finishing readjusting his coat when he noticed Dean was staring at him. 

Raising an eyebrow, he asked “What?” 

Dean licked his lips and asked “You like burgers?” 

Cas smiled in amusement as he straightened his coat, “I do.” 

Dean grinned, “Great, because I know a little place that serves the best burgers in the world.” He pulled out his winnings he got from Cas from his pocket, “I’ll buy.” 

Castiel laughed.

**Author's Note:**

> Thank you so much for reading!! Let me know what your thoughts are in the comments below!


End file.
